100+ Personal Questions To Ask a Guy

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Want to get to know someone on a deeper level? Looking for personal questions to ask a guy? Whether it’s your boyfriend or someone you’re dating / “seeing”, we’ve crafted 100+ personal questions to ask him, which will really bring you closer. Uh huh, we’re moving past the realms of superficial conversation and stepping things up a notch!

What Are Personal Questions?

So before we get started, let’s first establish what we mean by “personal questions to ask a guy.” I mean, what actually are personal questions? 

Essentially, a personal question is something relating to the private aspect of that person’s life.

This means, personal questions are deeper questions – the kind of questions you couldn’t ask just anyone. The two of you have to have some trust in your relationship in order for him to be able to answer them properly and honestly.

This also means, however, that you can also use personal questions to build trust and become closer with a person. (Woohoo.) And thus, a deeper connection will form.

How To Ask a Guy Personal Questions

So next comes the question of, well, how to ask personal questions.

Do you just come out with them? Well, yes, essentially. You want it to be as casual as you possibly can. HOWEVER – the moment has to be right!

I mean, you wouldn’t ask a guy personal questions in the middle of the supermarket… (Yikes!) And I’d definitely steer well clear if the guy’s left you on read. No, no, no.

Instead, we’re thinking more – when you’re cuddled up in bed, the lights off, the night still young, and are looking for interesting conversation. You see?

Another key essential when it comes to personal questions to ask a guy – is that you too, have to be willing to share. In fact, sharing something on the topic first, can be a great way to introduce that question back to them.

So let go of your own trust issues, if you’re looking to form stronger relationships from here.

Be respectful if someones not comfortable talking about something, of course…

But make it easier by easing into the questions, starting with the “lighter” personal questions to ask a guy, before building them up more and more, as time goes on.

How to get to know someone better

Why Is It Good To Ask Personal Questions?

Asking personal questions and opening up around these kind of topics not only creates interesting conversation as mentioned, but it also really builds your bond and increases emotional intimacy.

Asking personal questions also creates an outlet for the other person, who’s then able to speak openly and freely about things that they perhaps, otherwise would have kept inside.

It’s healthy, and in many ways, actually therapeutic!

It’s also very satisfying when you know that you can talk to a person about anything and everything. That’s really quite special.

So it’s well worth dabbling into more of these personal questions to ask a guy, as I just know, you’ll be pleasantly surprised by just how great of an impact it has!

100+ Personal Questions To Ask A Guy

Without further ado, here’s 100+ personal questions to ask a guy – to get the inspiration flowing.

Remember – this should just be a base, to start to get you thinking of different personal questions you could ask a guy.

As you read through – notice which questions you like, which ones intrigue you the most. And also encourage other questions it makes you think of, then be sure to ask these too!

Don’t ask all these questions in one go (of course!) You don’t want to be coming on too strong.

Just make a note of the kind of things you’d be interested in asking – then ask them at the right time! Got it? Awesome. Then let’s get stuck in…

Personal Questions To Ask a Guy

1) What are you passionate about? And why are you so passionate about it? Where does this passion come from? And what does it mean to you?

2) Do you think about the future much? What about it excites you and what about it scares you? And why?

3) Where do you see yourself in 5 years time? Or more specifically, where would you most like to see yourself, do you think you will get there, and what would stand in your way of not?

4) Are there any things you wish you had the courage to do? Or any things you secretly want to do or have, but are too afraid / embarrassed to put yourself out there and say it?

(FUN FACT: Only 20% of people consider themselves to be courageous, so it will be interesting to hear what he says about this one, for sure!)

5) What kind of life do you want to live? What would a perfect future look like to you?

6) How do you feel in yourself and your life right now? Is there anything you wish you could change, or anything you wish you had?

7) Do you usually express how you feel, or repress your emotions / keep your emotions hidden? And why do you think this is?

8) What emotions do you find most difficult to deal with? And what kind of feelings do you crave the most?

9) When are you happiest and what makes you feel truly happy?

Deep questions to get to know someone

Let’s Keep Them Coming…

10) What makes you feel loved? What is your love language? And how do you think that affects your relationships?

11) What have your past relationships taught you? And do you have any regrets about how you’ve behaved in relationships before?

(If you’re in a relationship with the guy you’re asking these personal questions to – you can also ask the same questions about your current relationship, too. This may sound like a tough relationship question, but it will only make the two of you grow.)

12) What other times / situations have taught you the most about yourself?

13) What have been the most challenging times of your life? And how did you get through them? 

14) Do you think you’re fully healed from the past? How did you heal? And what did it take? What did you have to do to get through it?

15) What has been the best phase of your life so far?

16) Are you where you thought you’d be at this current stage in your life? In what ways has it met your expectations and in what ways is it different? 

17) Do you want to have children? Why is / isn’t this important to you?

18) What do you think is most important when it comes to parenting? And what kind of parent do you think you’d be?

Personal Questions To Ask a Guy

19) What is your personal philosophy to life? 

20) What do you wish you could tell your former self?

21) Do you think you were put on this earth for a reason? What’s your purpose or mission in life?

22) What values, morals and beliefs do you pride yourself in? Where did they come from, and why is this important to you?

23) Do you have any role models in your life? If so, who? And how have they influenced you?

24) How would you define yourself? And what defines you the most? What makes you, you?

25) What areas of self improvement do you think you need to work on? And how easy do you think it would be to work on / improve in that area?

How well do you know him?

How Well Do You Know Him?

How well do you know your boyfriend? Or the guy you’re seeing? How many of these questions do you already know the answers to? Try these 365+ how well do you know me questions if you like the idea of this! In the meantime, let’s keep these personal questions flowing…

26) In which moments of your life, have you been the most scared?

27) What are you afraid of? What are some of your deepest fears? And let’s go beyond snakes or spiders!

28) What are you most proud of? This can be relating to the things you’ve done, and / or the person you’ve become.

29) What do you like about yourself? What do you think are the best things about you?

(Some of these questions, he may not know the answer too. And maybe you don’t know the answer too! So here’s 50+ questions to get to know yourself better, to increase your own personal self awareness, before we move on!)

30) How do you think others see you? And what things do you think they perhaps, don’t see about you?

31) What’s your biggest insecurity? Dig deep with this one, sharing things people also don’t know.

32) What has been the most beautiful thing you’ve ever seen or experienced?

33) What are you the most thankful for in your life? And how much do you focus on, and appreciate this?

Let’s Keep Digging Deeper…

34) What’s the biggest decision you’ve ever had to make? How hard was it to make this decision? And do you think you did the right thing? How did everything then work out?

35) How do you feel about commitment? It is something that scares you, or makes you feel settled / safe?

Not-So-Fun-Fact: 34% of millennials suffer from commitment issues because they have been hurt in a past relationship. And 29% of millennials lack the confidence to navigate through a relationship for more extended periods. So conversations about commitment could be one of the most valuable personal questions to ask a guy!

36) Have you ever felt unsafe in your life? In which moments? What happened?

37) What do you do when life gets difficult? How hard does it affect you? And what kind of things do you / would you find the most challenging?

38) Do you think you have many negative thoughts? In which moments do they most often come? And how do you deal with them? How much influence do they have over you?

39) If you died tomorrow, what would you have wished you’d have done?

40) What would you want to be known for, once your life is over? What legacy (if any) would you like to leave, and how important is this to you? Plus – why?

41) What do you think makes you different to other people?

42) How would you describe your personality?

Personal Questions To Ask a Guy

Personal Questions To Ask a Guy

43) How would you define success? And what does success mean to you?

44) Do you feel your age? And how does it feel to be your age? Are you conscious of your age and time? How much pressure do you put on yourself when it comes to doing things or having things at certain times?

(I mean, we all know there’s dating and relationship milestones, but these aren’t the only ones!)

45) What is your relationship like with your parents? Look at both the positives and the negatives.

46) How have your parents influenced the person that you’ve become?

47) What is the first thing you think of when you wake up and the last thing on your mind when you go to bed at night? Generally speaking anyway.

48) What motivates you in life? And really gets you out of bed every morning?!

49) What do you like and dislike about your work? And what do you think your friends and family think about what you do? Has this ever influenced your career decisions?

50) How do you feel about the friends you have in your life? Are they a positive or negative influence? How similar are they to you, and in what ways? And how much do you trust them?

Personal Questions To Ask a Guy

We’re half way through! Is this filling you ideas with personal questions to ask a guy? Do you see how asking these questions, will bring the two of you so much closer, whilst making you learn more about each other? It’s pretty neat, huh? Keep learning, keep growing!

51) What makes you feel the most stressed? And how do you relax when you feel stressed?

52) Have you ever had any mental health issues?

53) What about any physical health issues, or scares?

54) How important is money to you? Why / why not? And how much money do you think you need to have to live the kind of life you want to live?

55) How important is family to you? Expand on this more!

56) What quality do you admire the most in others? And why?

57) Do you think you hold grudges easily? How do you respond to someone who mistreats you? And what does it take in order for you to forgive mistreatment? 

58) How to do you feel about change in life? Is it something you dread or embrace? And why? What have been the best and worst changes that have come in your life so far? And what did that show you?

questions to bring you closer

Let’s Keep Them Coming…

59) How do you feel about taking risks? And what’s the biggest risk you’ve taken? Did it pay off? 

60) What’s the biggest thing you’ve ever given up?

61) What makes you angry? And how easily do you get angry? How do you act when you’re angry?

62) Are you a jealous person? What kind of things or situations make you feel jealous and why? (Be honest!)

63) What’s the nicest thing you’ve ever done for someone? Or nice things you do pretty consistently? How nice of a person do you think you are? And how much do you value kindness?

64) How open do you think you are as a person? Do you think that opening up makes you more vulnerable or do you feel pretty comfortable with it? Explain why!

65) How would you describe your childhood? Did you have more positive or negative experiences?

66) Have you ever had any family fall-outs or dramas? Are there any left unresolved? In what ways? And what are your thoughts on all of this?

67) How difficult / easy do you find it to trust people? And why?

Personal Questions To Ask a Guy

68) What does love mean to you? How easily do you fall in love? And how do you know once you are in love? (As here’s the common signs he’s falling for you!)

69) What would make you fall out of love with a person? And are you afraid of someone that you love, falling out of love with you?

70) Have you ever had temptations to cheat on a partner? Or cheated on someone in a relationship before? Why? And how did this make you feel?

71) What’s the biggest lie you’ve ever told? And how often do you tell lies? (For this question, you actually have to be honest about it though… of course!)

72) What do you think are the best things money can buy? And the best things money can’t buy?

73) Are there any things you really want to do in your life? Like, bucket-list experiences? And why do these things appeal to you so much? What do you think are the chances of you actually doing them? (Remember, you should have your very own singles bucket list you should be working through right now, if you don’t yet have a significant other in your life, too!)

74) What simple change could you make in your life that would have the biggest positive impact?

75) What’s one thing people have tried to tell you, but you wouldn’t listen to or learn from, until you went though it yourself?

What New Things Are You Learning?

Don’t forget, with all of these personal questions to ask a guy – you want to keep sharing your answers to these topics too. It’s not just a one-way thing. Encourage interesting, deeper conversation!

76) What do you judge people for that you probably shouldn’t? Do you think you’re a judgemental person? And why / why not? Where has this come from?

77) Do you think you more often face your fears, or forget that you have them? What stops you from getting outside your comfort zone and how much does this play on your mind?

78) In which situations are you the most and least yourself? Have there ever been times where you feel like you lost yourself? And what’s made you come out of your shell the most?

79) How much do you value or need “alone time”? Do you ever get lonely? How lonely? And how do you deal with loneliness?

80) Do you think you are a more “live in the moment”, “look forward to the future” or “stuck in the past” kind of person? And why?

81) What kind of people do you think you click best with? And how compatible do you think we are? (Of course only ask this once you’ve gotten to know him a little more and had a fair few dates!)

82) What kind of people do you dislike? And why?

Personal Questions To Ask a Guy

Personal Questions To Ask a Guy

83) Have you ever lost respect for a person? And if so – why, what did they do? Plus what makes you respect a person? What kind of things earn your respect, and is it hard to earn or more automatically a given?

84) What kind of things do you think are unforgivable?

85) What things or people, make you feel good about yourself? And how? How do you also make yourself feel good about yourself? And how easy is this to do?

86) What things would you never do, for any amount of money?

87) How good are you at saving money and what things do you think are a waste of money?

88) Whats your most prized possession? Or little things that you’d actually struggle to live without?

89) What’s the wildest things you’ve ever done? And how did they make you feel in that moment? What kind of things make you feel the MOST ALIVE?!

90) What are your political beliefs? And what kind of changes would you implement if you were running the country? Plus why? (This question can be quite a big, but interesting one!)

91) What are your spiritual and / or religious beliefs? Let’s talk more about that!

We’re Into The Final Set of Questions…

92) Do you think that people more underestimate or overestimate you? And why?

93) What do you think that many people don’t understand / know about you? And how may most people be unable to relate to a certain thing about you?

94) When was the last time you cried? And what over?

INTERESTING STUDY: Apparently, the average woman cries 30 to 64 times a year, compared to men who cry 5 to 17 times. (Although that depends how many times they’ve watched “Remember Me” or “A Fault In Our Stars” in the last year, right?! :P)

95) What’s the worst thing that you’ve ever done to someone? Is there anything you’re ashamed or, or disappointed with yourself about?

96) What will you never allow someone to do to you? Or never allow someone to do to you again (if it’s already happened before, in the past)?

97) Have you ever been addicted to anything? To what level? And how did you overcome the addiction or change your behaviour? How hard was it?

DID YOU KNOW: Obsessive Love Disorder is even a thing?! Uh huh. People can actually be addicted to love, although I don’t imagine you’ll get many of those confessions!

98) If you could re-live one moment of your life, what would it be and why? (Got a few? Share more!)

99) What do you wish you knew more about? Or something you wish you were better at?

100) What’s one thing you’ve never told someone about yourself before?

That’s All For This One

So there we have it – 100 personal questions to ask a guy, to get to know him better and strengthen your bond further.

Liked these? Feel like he’s opening up more? Then don’t be afraid to ease into deeper questions to ask a guy. It will always only bring you closer, and don’t forget – these can still be mixed up with more light-hearted funny questions too!

I hope this has filled you with ideas for cute chats and conversation starters.

Take care!


Good questions to ask a guy
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Ella Stearn
Ell is a Breakup, Dating & Relationship Specialist & Coach, with over 3 million annual readers, globally. As the Creator of Forgetting Fairytales, her mission is to help you learn to love yourself, find the right person to give your love to, then make it a love that truly lasts.

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